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T2859

Sigma-Aldrich

Tamoxifen

powder, suitable for cell culture, BioReagent

Synonym(s):

Tamoxifen, (Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine

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About This Item

Linear Formula:
C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
CAS Number:
10540-29-1
Molecular Weight:
371.51
MDL number:
MFCD00010454
UNSPSC Code:
12352207
NACRES:
NA.76

product name

Tamoxifen, powder, Suitable for cell culture

Quality Level

200

Assay

≥99%

form

powder

storage condition

protect from light

mp

97-98 °C (lit.)

solubility

H2O: insoluble <0.1% at 20 °C
chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow
2-propanol: soluble
DMSO: soluble
ethanol: soluble
methanol: soluble
propylene glycol: soluble

antibiotic activity spectrum

neoplastics

Mode of action

cell membrane | interferes
enzyme | inhibits

shipped in

ambient

storage temp.

2-8°C

SMILES string

CC\C(c1ccccc1)=C(/c2ccccc2)c3ccc(OCCN(C)C)cc3

InChI

1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-

InChI key

NKANXQFJJICGDU-QPLCGJKRSA-N

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General description

Tamoxifen (TAM) an antimicrobial agent is also a selective estrogen response modifier (SERM) that is used to prevent and treat breast cancer. It was first introduced by AstraZeneca as effective therapeutic and preventive agent against estrogen-positive breast cancer. As an antibiotic, TAM has shown a direct inhibitory action on the growth of Staphylococcus aureus, methicillin-resistant S. aureus (MRSA) strains, and M. tuberculosis.1 It is metabolized to active metabolites 4-hydroxytamoxifen (4-OHT) and endoxifen by cytochrome P450 isoforms CYP2D6 and CYP3A4. TAM is also a protein kinase C inhibitor and an anti-angiogenetic factor.

Application

Contribution of metabolic effects of TAM in increasing drug resistance was studied in MCF-7 and MCF7-TAM cell lines. 4-hydroxytamoxifen was used to examine calcium influx in human-induced pluripotent stem cell-derived cardiomyocytes (iPSC-CMs) modeled on Duchenne Muscular Dystrophy (DMD).

Biochem/physiol Actions

Active metabolites of TAM act as estrogen antagonists inmammary glands and block VEGF production in breast cancer cells. TAM is known toinhibit mitochondrial function, causing increased glycolysis and lactateproduction. 4-hydroxytamoxifen treatment of iPSC-CMs increased cellsurvival, decreased beating rate and increased beating velocity.

As an antibiotic, TAM increases membrane permeabilityand is active against Gram-positive and Gram- negative bacterial strains. It actsas both bactericidal and bacteriostatic agent.
Protein kinase C inhibitor. Induces apoptosis in human malignant glioma cell lines. Tamoxifen and its metabolite 4-hydroxytamoxifen are selective estrogen response modifiers (SERMs) that act as estrogen antagonists in mammary gland. Blocks estradiol-stimulated VEGF production in breast tumor cells.

Preparation Note

Tamoxifen is soluble in chloroform at 50 mg/ml and yields a clear, colorless to faint yellow solution. Stock solutions of tamoxifen can also be prepared in DMSO at 10 mM and are stable when stored at -20° C in the dark. It is also soluble in methanol, ethanol, 2-propanol and propylene glycol. It is practically insoluble in water (solubility is <0.01%, 20° C). Solutions are sensitive to UV light.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H350,H360,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tamoxifen treatment ameliorates contractile dysfunction of Duchenne muscular dystrophy stem cell-derived cardiomyocytes on bioengineered substrates
Foster Birnbaum, Asuka Eguchi, Gaspard Pardon, Alex C. Y. Chang & Helen M. Blau
NPJ Regenerative medicine null
Automated online monitoring of lactate and pyruvate in tamoxifen resistant MCF-7 cells using sequential-injection capillary electrophoresis with contactless conductivity detection (SI-CE-C4D) and correlation with MCT1 and MCT4 genes expression
Ala A. Alhusban, Lama A. Hamadneh, Aliaa I. Shallan & Ola A. TarawnehORCID Icon
Journal of Liquid Chromatography and Related Technologies (2022)

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